EP2101826B1 - Radiolabelled peptide based compounds and uses thereof - Google Patents

Radiolabelled peptide based compounds and uses thereof Download PDF

Info

Publication number: EP2101826B1
Authority: EP; European Patent Office
Prior art keywords: compound; angiogenesis; pet; based compounds; carbon
Prior art date: 2006-12-11
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Not-in-force

Application number

EP07860908A

Other languages

German (de)

English (en)

French (fr)

Other versions

EP2101826A2 (en

Inventor

Torgrim Engell

Steven Fairway

Ingrid Henriksen

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

GE Healthcare AS

Original Assignee

GE Healthcare AS

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2006-12-11

Filing date

2007-12-11

Publication date

2010-06-23

2007-12-11 Application filed by GE Healthcare AS filed Critical GE Healthcare AS

2007-12-11 Priority to PL07860908T priority Critical patent/PL2101826T3/pl

2009-09-23 Publication of EP2101826A2 publication Critical patent/EP2101826A2/en

2010-06-23 Application granted granted Critical

2010-06-23 Publication of EP2101826B1 publication Critical patent/EP2101826B1/en

Status Not-in-force legal-status Critical Current

2027-12-11 Anticipated expiration legal-status Critical

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 34
108090000765 processed proteins & peptides Proteins 0.000 title abstract description 15
201000010099 disease Diseases 0.000 claims abstract description 14
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 14
238000003745 diagnosis Methods 0.000 claims abstract description 5
230000033115 angiogenesis Effects 0.000 claims description 16
238000000034 method Methods 0.000 claims description 11
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
229910052799 carbon Inorganic materials 0.000 claims description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
206010028980 Neoplasm Diseases 0.000 claims description 6
241001465754 Metazoa Species 0.000 claims description 4
229940079593 drug Drugs 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 4
229910052757 nitrogen Chemical group 0.000 claims description 4
239000012217 radiopharmaceutical Substances 0.000 claims description 4
229940121896 radiopharmaceutical Drugs 0.000 claims description 4
230000002799 radiopharmaceutical effect Effects 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
201000011510 cancer Diseases 0.000 claims description 3
230000000694 effects Effects 0.000 claims description 3
238000003384 imaging method Methods 0.000 claims description 3
229910052760 oxygen Chemical group 0.000 claims description 3
239000001301 oxygen Chemical group 0.000 claims description 3
239000002671 adjuvant Substances 0.000 claims description 2
238000001514 detection method Methods 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
238000001727 in vivo Methods 0.000 claims description 2
238000011503 in vivo imaging Methods 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
239000000203 mixture Substances 0.000 claims description 2
238000012544 monitoring process Methods 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
238000002600 positron emission tomography Methods 0.000 abstract description 7
238000002059 diagnostic imaging Methods 0.000 abstract description 6
230000004054 inflammatory process Effects 0.000 abstract description 6
206010061218 Inflammation Diseases 0.000 abstract description 5
201000009273 Endometriosis Diseases 0.000 abstract description 3
208000007766 Kaposi sarcoma Diseases 0.000 abstract description 3
230000003211 malignant effect Effects 0.000 abstract description 3
206010039073 rheumatoid arthritis Diseases 0.000 abstract description 3
238000002560 therapeutic procedure Methods 0.000 abstract description 3
208000019622 heart disease Diseases 0.000 abstract description 2
230000015572 biosynthetic process Effects 0.000 description 5
210000004027 cell Anatomy 0.000 description 5
239000002870 angiogenesis inducing agent Substances 0.000 description 4
210000002469 basement membrane Anatomy 0.000 description 4
210000004204 blood vessel Anatomy 0.000 description 4
210000002889 endothelial cell Anatomy 0.000 description 4
210000001519 tissue Anatomy 0.000 description 4
0 CCC*C(CCCC(NCCCC#C)=O)=O Chemical compound CCC*C(CCCC(NCCCC#C)=O)=O 0.000 description 3
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 3
238000010647 peptide synthesis reaction Methods 0.000 description 3
102000004196 processed proteins & peptides Human genes 0.000 description 3
102000005962 receptors Human genes 0.000 description 3
108020003175 receptors Proteins 0.000 description 3
DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
201000001320 Atherosclerosis Diseases 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
108010073929 Vascular Endothelial Growth Factor A Proteins 0.000 description 2
102000005789 Vascular Endothelial Growth Factors Human genes 0.000 description 2
108010019530 Vascular Endothelial Growth Factors Proteins 0.000 description 2
230000000975 bioactive effect Effects 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000002372 labelling Methods 0.000 description 2
210000004185 liver Anatomy 0.000 description 2
210000000056 organ Anatomy 0.000 description 2
239000002243 precursor Substances 0.000 description 2
102000004169 proteins and genes Human genes 0.000 description 2
108090000623 proteins and genes Proteins 0.000 description 2
ZNKJYZHZWALQNX-UHFFFAOYSA-N 1-chloro-3-fluoropropan-2-ol Chemical compound FCC(O)CCl ZNKJYZHZWALQNX-UHFFFAOYSA-N 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
OIFAHDAXIUURLN-UHFFFAOYSA-N 2-(fluoromethyl)oxirane Chemical compound FCC1CO1 OIFAHDAXIUURLN-UHFFFAOYSA-N 0.000 description 1
206010003571 Astrocytoma Diseases 0.000 description 1
206010006187 Breast cancer Diseases 0.000 description 1
208000026310 Breast neoplasm Diseases 0.000 description 1
YNQLUTRBYVCPMQ-UHFFFAOYSA-N CCc1ccccc1 Chemical compound CCc1ccccc1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
208000006332 Choriocarcinoma Diseases 0.000 description 1
206010009900 Colitis ulcerative Diseases 0.000 description 1
206010009944 Colon cancer Diseases 0.000 description 1
208000001333 Colorectal Neoplasms Diseases 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
206010018338 Glioma Diseases 0.000 description 1
206010021143 Hypoxia Diseases 0.000 description 1
206010061216 Infarction Diseases 0.000 description 1
206010058467 Lung neoplasm malignant Diseases 0.000 description 1
206010027476 Metastases Diseases 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
206010029260 Neuroblastoma Diseases 0.000 description 1
206010033128 Ovarian cancer Diseases 0.000 description 1
206010061535 Ovarian neoplasm Diseases 0.000 description 1
238000012879 PET imaging Methods 0.000 description 1
206010061902 Pancreatic neoplasm Diseases 0.000 description 1
102000035195 Peptidases Human genes 0.000 description 1
108091005804 Peptidases Proteins 0.000 description 1
206010060862 Prostate cancer Diseases 0.000 description 1
208000000236 Prostatic Neoplasms Diseases 0.000 description 1
201000004681 Psoriasis Diseases 0.000 description 1
208000017442 Retinal disease Diseases 0.000 description 1
206010038923 Retinopathy Diseases 0.000 description 1
206010039710 Scleroderma Diseases 0.000 description 1
201000010208 Seminoma Diseases 0.000 description 1
208000000453 Skin Neoplasms Diseases 0.000 description 1
201000006704 Ulcerative Colitis Diseases 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000009471 action Effects 0.000 description 1
150000001412 amines Chemical group 0.000 description 1
125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 description 1
230000000259 anti-tumor effect Effects 0.000 description 1
230000003143 atherosclerotic effect Effects 0.000 description 1
210000000481 breast Anatomy 0.000 description 1
208000037976 chronic inflammation Diseases 0.000 description 1
230000006020 chronic inflammation Effects 0.000 description 1
230000002301 combined effect Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
206010012601 diabetes mellitus Diseases 0.000 description 1
210000004696 endometrium Anatomy 0.000 description 1
229940088598 enzyme Drugs 0.000 description 1
208000007565 gingivitis Diseases 0.000 description 1
208000005017 glioblastoma Diseases 0.000 description 1
201000011066 hemangioma Diseases 0.000 description 1
206010073071 hepatocellular carcinoma Diseases 0.000 description 1
206010020718 hyperplasia Diseases 0.000 description 1
230000002390 hyperplastic effect Effects 0.000 description 1
230000007954 hypoxia Effects 0.000 description 1
239000012216 imaging agent Substances 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
230000007574 infarction Effects 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
102000006495 integrins Human genes 0.000 description 1
108010044426 integrins Proteins 0.000 description 1
230000000302 ischemic effect Effects 0.000 description 1
238000009533 lab test Methods 0.000 description 1
230000003902 lesion Effects 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
201000005202 lung cancer Diseases 0.000 description 1
208000020816 lung neoplasm Diseases 0.000 description 1
210000002540 macrophage Anatomy 0.000 description 1
208000002780 macular degeneration Diseases 0.000 description 1
208000015486 malignant pancreatic neoplasm Diseases 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
201000001441 melanoma Diseases 0.000 description 1
230000009401 metastasis Effects 0.000 description 1
238000013508 migration Methods 0.000 description 1
230000005012 migration Effects 0.000 description 1
230000011278 mitosis Effects 0.000 description 1
210000004165 myocardium Anatomy 0.000 description 1
230000014399 negative regulation of angiogenesis Effects 0.000 description 1
238000009206 nuclear medicine Methods 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
201000008482 osteoarthritis Diseases 0.000 description 1
150000002924 oxiranes Chemical class 0.000 description 1
201000002528 pancreatic cancer Diseases 0.000 description 1
208000008443 pancreatic carcinoma Diseases 0.000 description 1
208000030613 peripheral artery disease Diseases 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000008569 process Effects 0.000 description 1
230000002062 proliferating effect Effects 0.000 description 1
210000002307 prostate Anatomy 0.000 description 1
230000017854 proteolysis Effects 0.000 description 1
229940024999 proteolytic enzymes for treatment of wounds and ulcers Drugs 0.000 description 1
238000001959 radiotherapy Methods 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000003248 secreting effect Effects 0.000 description 1
230000028327 secretion Effects 0.000 description 1
201000000849 skin cancer Diseases 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
238000010532 solid phase synthesis reaction Methods 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
-1 t-butoxycarbonyl Chemical group 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000000844 transformation Methods 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
230000004862 vasculogenesis Effects 0.000 description 1
239000013598 vector Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
230000029663 wound healing Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/13—Labelling of peptides
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/08—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/08—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins
- A61K51/088—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins conjugates with carriers being peptides, polyamino acids or proteins
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system

Definitions

the present invention relates to radiolabelled peptide-based compounds and their use for diagnostic imaging using positron emission tomography (PET).
PET positron emission tomography
Such compounds may thus be used for diagnosis or therapy of, for example, malignant diseases, heart diseases, endometriosis, inflammation-related diseases, rheumatoid arthritis and Kaposi's sarcoma.
radiolabelled bioactive peptides for diagnostic imaging is gaining importance in nuclear medicine.
Biologically active molecules which selectively interact with specific cell types are useful for the delivery of radioactivity to target tissues.
radiolabelled peptides have significant potential for the delivery of radionuclides to tumours, infarcts, and infected tissues for diagnostic imaging and radiotherapy.
18 F with its half-life of approximately 110 minutes, is the positron-emitting nuclide of choice for many receptor imaging studies. Therefore, 18 F-labelled bioactive peptides have great clinical potential because of their utility in PET to quantitatively detect and characterise a wide variety of diseases.
New blood vessels can be formed by two different mechanisms: vasculogenesis or angiogenesis.
Angiogenesis is the formation of new blood vessels by branching from existing vessels.
the primary stimulus for this process may be inadequate supply of nutrients and oxygen (hypoxia) to cells in a tissue.
the cells may respond by secreting angiogenic factors, of which there are many; one example, which is frequently referred to, is vascular endothelial growth factor (VEGF).
VEGF vascular endothelial growth factor
These factors initiate the secretion of proteolytic enzymes that break down the proteins of the basement membrane, as well as inhibitors that limit the action of these potentially harmful enzymes.
the other prominent effect of angiogenic factors is to cause endothelial cells to migrate and divide.
the combined effect of loss of attachment and signals from the receptors for angiogenic factors is to cause the endothelial cells to move, multiply, and rearrange themselves, and finally to synthesise a basement membrane around the new vessels.
Angiogenesis is prominent in the growth and remodelling of tissues, including wound healing and inflammatory processes. Tumours must initiate angiogenesis when they reach millimetre size in order to keep up their rate of growth. Angiogenesis is accompanied by characteristic changes in endothelial cells and their environment. The surface of these cells is remodelled in preparation for migration, and cryptic structures are exposed where the basement membrane is degraded, in addition to the variety of proteins which are involved in effecting and controlling proteolysis. In the case of tumours, the resulting network of blood vessels is usually disorganised, with the formation of sharp kinks and also arteriovenous shunts. Inhibition of angiogenesis is also considered to be a promising strategy for antitumour therapy.
angiogenesis is also very promising for diagnosis, one example being malignant disease, but the concept also shows great promise in inflammation and a variety of inflammation-related diseases, including atherosclerosis, the macrophages of early atherosclerotic lesions being potential sources of angiogenic factors.
WO 2003/006491 describes peptide-based compounds which target integrin receptors associated with angiogenesis.
International application PCT/GB2004/001052 describes methods suitable for labelling biologically active vectors with 18 F.
further peptide-based compounds having utility for diagnostic imaging techniques such as PET.
the present invention relates to peptide-based compounds and their use for diagnostic imaging using PET.
the 18 F peptide based compounds discussed herein show a biodistribution (less binding in liver and other organs) that is about 15% higher in comparison to any relatively successful prior agents developed.
One embodiment of the present invention encompasses a compound of formula (1), wherein X is a carbon or nitrogen.
Yet another embodiment of the invention entailes a compound of formula 2, wherein Y is a carbon or oxygen and X is a nitrogen or carbon.
Still a further embodiment of the invention depicts a radiopharmaceutical composition
a radiopharmaceutical composition comprising an effective amount of a compound of formula 1 or 2, together with one or more pharmaceutically acceptable adjuvants, excipients or diluents.
Yet another embodiment of the present invention depicts a compound of formula 1 or 2 for medical use particularly in the in vivo diagnosis or imaging, for example by PET, of a disease or condition associated with angiogenesis.
diseases and conditions associated with angiogenesis includes those diseases and conditions referred to below. Reference is also made in this regard to WO 98/47541 .
Diseases and conditions associated with angiogenesis include different forms of cancer and metastasis, for example, breast, skin, colorectal, pancreatic, prostate, lung or ovarian cancer.
inflammation for example, chronic inflammation
atherosclerosis for example, atherosclerosis
rheumatoid arthritis for example, gingivitis
angiogenesis diseases and conditions associated with angiogenesis are arteriovenous alformations, astrocytomas, choriocarcinomas, glioblastomas, gliomas, hemangiomas (childhood, capillary), hepatomas, hyperplastic endometrium, ischemic myocardium, endometriosis, Kaposi sarcoma, macular degeneration, melanoma, neuroblastomas, occluding peripheral artery disease, osteoarthritis, psoriasis, retinopathy (diabetic, proliferative), scleroderma, seminomas and ulcerative colitis.
Still another embodiment of the present invention depicts a use of a compound of formula 1 or 2 for the manufacture of a radiopharmaceutical for use in the method of in vivo imaging.
Yet another embodiment of the present invention shows a method of generating an image of a human or animal body comprising administering a compound of claim 1 or 2 to said body and generating an image of at least a part of said body to which said compound has distributed using PET.
Another embodiment of the present invention shows a method of monitoring the effect of treatment of a human or animal body with a drug to combat a condition associated with cancer, preferably angiogenesis, said method comprising administering to said body a compound of formula 1 or 2 and detecting the uptake of said compound by cell receptors said administration and detection optionally but preferably being effected before, during and after treatment with said drug.
a precursor for the novel 18 F peptide based compounds are made from a reaction between A (available from Bachem) and a by-product from the synthesis of B (mono-alkylated by-product). See Scheme 1 below.
novel 18 F peptide based compound disclosed herein (4) wherein Z is carbon is made by reacting the precursor (3) shown above with 18 F epifluorohydrin or with 1-fluoro-3-chloro-propan-2-ol. See Scheme 2 below.
novel angiogenesis 18 F peptide based compounds have a superior biological profile/properties compared to other compounds.
the novel 18 F peptide based compounds discussed herein show a biodistribution (less binding in liver and other organs) that is about 15% higher in comparison to any relatively successful prior agents developed.

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Organic Chemistry (AREA)
Epidemiology (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Optics & Photonics (AREA)
Physics & Mathematics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Rheumatology (AREA)
Analytical Chemistry (AREA)
Biochemistry (AREA)
Endocrinology (AREA)
Reproductive Health (AREA)
Immunology (AREA)
Pain & Pain Management (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Physical Education & Sports Medicine (AREA)
Biophysics (AREA)
Orthopedic Medicine & Surgery (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Peptides Or Proteins (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

EP07860908A 2006-12-11 2007-12-11 Radiolabelled peptide based compounds and uses thereof Not-in-force EP2101826B1 (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
PL07860908T PL2101826T3 (pl)	2006-12-11	2007-12-11	Znakowane izotopowo związki na bazie peptydów i ich zastosowania

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US86938206P	2006-12-11	2006-12-11
PCT/NO2007/000434 WO2008072973A2 (en)	2006-12-11	2007-12-11	Radiolabelled peptide based compounds and uses thereof

Publications (2)

Publication Number	Publication Date
EP2101826A2 EP2101826A2 (en)	2009-09-23
EP2101826B1 true EP2101826B1 (en)	2010-06-23

Family

ID=39252990

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
EP07860908A Not-in-force EP2101826B1 (en)	2006-12-11	2007-12-11	Radiolabelled peptide based compounds and uses thereof

Country Status (15)

Country	Link
US (1)	US20100322857A1 (pt)
EP (1)	EP2101826B1 (pt)
JP (1)	JP2010512310A (pt)
KR (1)	KR20090097868A (pt)
CN (2)	CN101563108B (pt)
AT (1)	ATE471724T1 (pt)
AU (1)	AU2007332210A1 (pt)
BR (1)	BRPI0720257A2 (pt)
CA (1)	CA2671564A1 (pt)
DE (1)	DE602007007362D1 (pt)
ES (1)	ES2346595T3 (pt)
MX (1)	MX2009006028A (pt)
PL (1)	PL2101826T3 (pt)
RU (1)	RU2009119917A (pt)
WO (1)	WO2008072973A2 (pt)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2011027584A1 (ja) *	2009-09-04	2011-03-10	国立大学法人京都大学	膵島イメージング用分子プローブ及びその使用

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2774378B2 (ja) *	1991-02-08	1998-07-09	ダイアテク，インコーポレイテッド	映像用テクネチウム−９９ｍ標識化ポリペプチド
CN1230441C (zh) *	2000-04-12	2005-12-07	安盛药业有限公司	结合整联蛋白的肽衍生物
GB0116815D0 (en) *	2001-07-10	2001-08-29	Nycomed Amersham Plc	Improved chelator conjugates
WO2003006491A2 (en) *	2001-07-10	2003-01-23	Amersham Health As	Peptide-based compounds for targeting intergin receptors
NO20030115D0 (no) *	2003-01-09	2003-01-09	Amersham Health As	Kontrastmiddel
GB0305704D0 (en) *	2003-03-13	2003-04-16	Amersham Plc	Radiofluorination methods

2007
- 2007-12-11 KR KR1020097012018A patent/KR20090097868A/ko not_active Withdrawn
- 2007-12-11 BR BRPI0720257-1A patent/BRPI0720257A2/pt not_active IP Right Cessation
- 2007-12-11 CA CA002671564A patent/CA2671564A1/en not_active Abandoned
- 2007-12-11 AT AT07860908T patent/ATE471724T1/de not_active IP Right Cessation
- 2007-12-11 ES ES07860908T patent/ES2346595T3/es active Active
- 2007-12-11 RU RU2009119917/15A patent/RU2009119917A/ru not_active Application Discontinuation
- 2007-12-11 CN CN200780045607XA patent/CN101563108B/zh not_active Expired - Fee Related
- 2007-12-11 EP EP07860908A patent/EP2101826B1/en not_active Not-in-force
- 2007-12-11 AU AU2007332210A patent/AU2007332210A1/en not_active Abandoned
- 2007-12-11 MX MX2009006028A patent/MX2009006028A/es active IP Right Grant
- 2007-12-11 CN CN2011101707069A patent/CN102321154A/zh active Pending
- 2007-12-11 PL PL07860908T patent/PL2101826T3/pl unknown
- 2007-12-11 WO PCT/NO2007/000434 patent/WO2008072973A2/en not_active Ceased
- 2007-12-11 US US12/517,413 patent/US20100322857A1/en not_active Abandoned
- 2007-12-11 DE DE602007007362T patent/DE602007007362D1/de active Active
- 2007-12-11 JP JP2009540191A patent/JP2010512310A/ja active Pending

Also Published As

Publication number	Publication date
AU2007332210A1 (en)	2008-06-19
CN101563108B (zh)	2012-07-18
RU2009119917A (ru)	2011-01-20
JP2010512310A (ja)	2010-04-22
WO2008072973A3 (en)	2009-05-22
BRPI0720257A2 (pt)	2014-02-25
WO2008072973A2 (en)	2008-06-19
ATE471724T1 (de)	2010-07-15
PL2101826T3 (pl)	2010-11-30
MX2009006028A (es)	2009-06-17
ES2346595T3 (es)	2010-10-18
CN101563108A (zh)	2009-10-21
CN102321154A (zh)	2012-01-18
EP2101826A2 (en)	2009-09-23
KR20090097868A (ko)	2009-09-16
CA2671564A1 (en)	2008-06-19
US20100322857A1 (en)	2010-12-23
DE602007007362D1 (de)	2010-08-05

Legal Events

Date	Code	Title	Description
2009-08-21	PUAI	Public reference made under article 153(3) epc to a published international application that has entered the european phase	Free format text: ORIGINAL CODE: 0009012
2009-09-23	17P	Request for examination filed	Effective date: 20090602
2009-09-23	AK	Designated contracting states	Kind code of ref document: A2 Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LT LU LV MC MT NL PL PT RO SE SI SK TR
2009-11-18	GRAP	Despatch of communication of intention to grant a patent	Free format text: ORIGINAL CODE: EPIDOSNIGR1
2010-03-26	GRAS	Grant fee paid	Free format text: ORIGINAL CODE: EPIDOSNIGR3
2010-04-28	DAX	Request for extension of the european patent (deleted)
2010-05-21	GRAA	(expected) grant	Free format text: ORIGINAL CODE: 0009210
2010-06-23	AK	Designated contracting states	Kind code of ref document: B1 Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LT LU LV MC MT NL PL PT RO SE SI SK TR
2010-06-30	REG	Reference to a national code	Ref country code: CH Ref legal event code: EP
2010-07-21	REG	Reference to a national code	Ref country code: IE Ref legal event code: FG4D
2010-08-05	REF	Corresponds to:	Ref document number: 602007007362 Country of ref document: DE Date of ref document: 20100805 Kind code of ref document: P
2010-08-13	REG	Reference to a national code	Ref country code: CH Ref legal event code: NV Representative=s name: ISLER & PEDRAZZINI AG
2010-09-08	REG	Reference to a national code	Ref country code: NL Ref legal event code: T3
2010-10-18	REG	Reference to a national code	Ref country code: ES Ref legal event code: FG2A Ref document number: 2346595 Country of ref document: ES Kind code of ref document: T3
2010-10-29	PG25	Lapsed in a contracting state [announced via postgrant information from national office to epo]	Ref country code: SE Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20100623 Ref country code: LT Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20100623
2010-11-25	LTIE	Lt: invalidation of european patent or patent extension	Effective date: 20100623
2010-11-30	PG25	Lapsed in a contracting state [announced via postgrant information from national office to epo]	Ref country code: AT Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20100623 Ref country code: SI Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20100623 Ref country code: FI Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20100623 Ref country code: LV Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20100623
2010-11-30	REG	Reference to a national code	Ref country code: PL Ref legal event code: T3
2011-01-31	PG25	Lapsed in a contracting state [announced via postgrant information from national office to epo]	Ref country code: EE Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20100623
2011-02-28	PG25	Lapsed in a contracting state [announced via postgrant information from national office to epo]	Ref country code: BE Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20100623 Ref country code: PT Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20101025 Ref country code: RO Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20100623 Ref country code: SK Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20100623 Ref country code: CY Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20100623 Ref country code: CZ Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20100623 Ref country code: IS Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20101023
2011-02-28	PGFP	Annual fee paid to national office [announced via postgrant information from national office to epo]	Ref country code: PL Payment date: 20101122 Year of fee payment: 4
2011-03-28	REG	Reference to a national code	Ref country code: HU Ref legal event code: AG4A Ref document number: E009199 Country of ref document: HU
2011-04-29	PG25	Lapsed in a contracting state [announced via postgrant information from national office to epo]	Ref country code: DK Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20100623
2011-04-29	PLBE	No opposition filed within time limit	Free format text: ORIGINAL CODE: 0009261
2011-04-29	STAA	Information on the status of an ep patent application or granted ep patent	Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT
2011-05-31	PG25	Lapsed in a contracting state [announced via postgrant information from national office to epo]	Ref country code: GR Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20100924
2011-06-01	26N	No opposition filed	Effective date: 20110324
2011-07-14	REG	Reference to a national code	Ref country code: DE Ref legal event code: R097 Ref document number: 602007007362 Country of ref document: DE Effective date: 20110323
2011-07-29	PG25	Lapsed in a contracting state [announced via postgrant information from national office to epo]	Ref country code: MC Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20101231
2011-12-30	PG25	Lapsed in a contracting state [announced via postgrant information from national office to epo]	Ref country code: MT Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20100623 Ref country code: IT Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20101211
2011-12-30	PGFP	Annual fee paid to national office [announced via postgrant information from national office to epo]	Ref country code: IT Payment date: 20101231 Year of fee payment: 4
2012-01-31	PGFP	Annual fee paid to national office [announced via postgrant information from national office to epo]	Ref country code: CH Payment date: 20111227 Year of fee payment: 5 Ref country code: ES Payment date: 20111226 Year of fee payment: 5 Ref country code: FR Payment date: 20120104 Year of fee payment: 5 Ref country code: HU Payment date: 20111125 Year of fee payment: 5 Ref country code: IE Payment date: 20111227 Year of fee payment: 5
2012-05-31	PGFP	Annual fee paid to national office [announced via postgrant information from national office to epo]	Ref country code: DE Payment date: 20111229 Year of fee payment: 5
2012-07-31	PGFP	Annual fee paid to national office [announced via postgrant information from national office to epo]	Ref country code: NL Payment date: 20120103 Year of fee payment: 5
2012-09-28	PG25	Lapsed in a contracting state [announced via postgrant information from national office to epo]	Ref country code: LU Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20101211 Ref country code: BG Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20100623
2012-10-31	PG25	Lapsed in a contracting state [announced via postgrant information from national office to epo]	Ref country code: TR Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20100623
2013-07-17	REG	Reference to a national code	Ref country code: NL Ref legal event code: V1 Effective date: 20130701
2013-07-31	REG	Reference to a national code	Ref country code: CH Ref legal event code: PL
2013-08-28	GBPC	Gb: european patent ceased through non-payment of renewal fee	Effective date: 20121211
2013-09-25	REG	Reference to a national code	Ref country code: IE Ref legal event code: MM4A
2013-09-27	REG	Reference to a national code	Ref country code: FR Ref legal event code: ST Effective date: 20130830
2013-09-30	PG25	Lapsed in a contracting state [announced via postgrant information from national office to epo]	Ref country code: BG Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20100923
2013-10-10	REG	Reference to a national code	Ref country code: DE Ref legal event code: R119 Ref document number: 602007007362 Country of ref document: DE Effective date: 20130702
2013-10-31	PG25	Lapsed in a contracting state [announced via postgrant information from national office to epo]	Ref country code: DE Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20130702 Ref country code: NL Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20130701 Ref country code: IE Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20121211 Ref country code: HU Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20121212 Ref country code: CH Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20121231 Ref country code: LI Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20121231
2013-11-29	PG25	Lapsed in a contracting state [announced via postgrant information from national office to epo]	Ref country code: FR Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20130102 Ref country code: GB Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20121211
2013-12-31	PG25	Lapsed in a contracting state [announced via postgrant information from national office to epo]	Ref country code: IT Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20121211
2014-02-28	PG25	Lapsed in a contracting state [announced via postgrant information from national office to epo]	Ref country code: PL Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20121211
2014-06-02	REG	Reference to a national code	Ref country code: ES Ref legal event code: FD2A Effective date: 20140602
2014-07-31	PG25	Lapsed in a contracting state [announced via postgrant information from national office to epo]	Ref country code: ES Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20121212

Publication	Publication Date	Title
US8563600B2 (en)	2013-10-22	Diagnostic compounds
US7521419B2 (en)	2009-04-21	Peptide-based compounds
US9956303B2 (en)	2018-05-01	Anti-met therapy for previously diagnosed cancer patients
EP2101826B1 (en)	2010-06-23	Radiolabelled peptide based compounds and uses thereof
Merrill et al.	2016	Synthesis and comparative evaluation of novel 64Cu-labeled high affinity cell-specific peptides for positron emission tomography imaging of tumor vasculature
EP3706809A1 (en)	2020-09-16	68ga- and 64cu -nodaga-e[c(rgdyk)]2 for use as pet tracers in the imaging of angiogenesis in humans
HK1118713B (en)	2015-08-07	Diagnostic compounds